Amy Heckerling’s Clueless offers some of the best humor, entertainment, and social insight the teen comedy genre has to offer. And, while that may sound like damning praise, I do not hesitate to suggest that the teen comedy is one of the most unfairly maligned and underappreciated genres in Hollywood if only because, like the similarly dismissed horror genre, so many of them are done so badly—without any wit, cleverness, and, most of all, humanity. The albatross of many teen comedies is that their makers have no respect for their characters, which makes them hard to care about. While Clueless gets plenty of laughs at the expense of its characters, it never looks down on them—or its audience, for that matter.

Heckerling made her name in the early 1980s as a rare female director working in Hollywood. Her breakout hit was Fast Times at Ridgemont High (1982), an uneven, but frequently hilarious and incisive teen comedy that set the bar for those that followed. Heckerling’s own career after that was extremely uneven, as her high-profile comedies Johnny Dangerously (1984) and National Lampoon’s European Vacation (1985) did moderate box office, but were generally panned by critics. A few years later she hit a box-office bulls-eye with Look Who’s Talking (1989), an amusing, but thin comedy in which the world is viewed through the eyes of a baby who thinks with Bruce Willis’ voice. A pointless sequel followed, also directed by Heckerling.

Those who saw a great deal of originality and playfully subversive potential in Heckerling at the beginnings of her career were disappointed to see her heading more and more toward the middle, which is why Clueless was such a refreshing change of pace. While it marked her return to the teen comedy genre where she had initially made her mark, her approach to the material was fresh and inventive enough that the film transcended comparisons to Fast Times.

In Clueless Heckerling took the basic plot of Jane Austen’s Emma and fashioned an updated social comedy set in the slightly surreal and clearly exaggerated world of pampered Beverly Hills teenagers. While some of her visual gags have come to full fruition (and beyond) in the years since the film’s theatrical release (teens walking around the school halls with cell phones seemingly glued to their ears), some of her more outlandish imagery, such as half the female school population having their surgically altered noses protected by splints, remains in the realm of hyperbole—if only barely.

Heckerling’s heroine is Cher (Alicia Silverstone), whose main goals in life are to look fabulous and meddle in other people’s affairs for their betterment. Her various “projects” include her frumpy debate teacher, Mr. Hall (Wallace Shawn), whom she gets together with her absent-minded environmental studies teacher, Miss Geist (Twink Caplan, one of the film’s producers). Her biggest challenge is the clueless new student, Tai (Brittany Murphy), who has been displaced from New Jersey and has no sense of style. Cher and her best friend, Dionne (Stacey Dash), change all that, but all the while Cher remains utterly oblivious to her own happiness. (How strange it is for a teen movie to be about a character who is constantly thinking about others and is genuinely interested in discovering what “doing good” really is, even if she doesn’t always do it.)

Cher narrates the movie in a tone that is consistently comical, yet strangely intimate. One of Heckerling’s masterstrokes is to take a character who would otherwise be the rich-bitch teen queen villainess and turn her into the movie’s misunderstood heroine. Cher’s relentless self-absorption is somehow twisted into a remarkable sense of introspection. It’s testament to both Heckerling’s clever writing and Silverstone’s first-rate, completely assured performance that Cher transcends the clichés of her character and becomes a genuinely sympathetic person for whom we root for even though, by any stretch of the imagination, she already has it all.

While the surface of Clueless is broadly entertaining, there are a number of things about it that set it apart from so many other movies of its ilk. In many ways, it is a playfully subversive riff on the “teen sex film,” a label applied by film scholar Robin Wood to the glut of teenage movies that filled cinemas throughout the 1980s (Fast Times being one of the exemplars). For example, while sex is certainly a topic of conversation in Clueless, it by no means dominates the story (despite her beauty and desirability, Cher is a virgin who is saving herself for the right guy—another narrative anomaly). There is also the inclusion of a gay teen character (Justin Walker), which was particularly rare at the time. And, because all the main characters are girls, the film doesn’t fall into the hunter/hunted dichotomy that privileges the male point of view and, by proxy, tends to reduce female characters to objects to be won (a trait typical of many teen films to varying degrees, from The Last American Virgin, to Porky’s, to American Pie).

Lastly, while most teen movies either repress parents completely or turn them into comical buffoons, Clueless derives some of its most emotionally endearing moments from scenes between Cher and her tough-talking, but soft-hearted litigator father (Dan Hedaya). To everyone else, he is someone to be feared, but Cher just sees him as “Daddy.” And, while this does infantilize Cher to a certain extent, it is made clear numerous times that he needs her as much as she needs him (she is constantly trying to get him to eat healthy, take his vitamins, not work so hard, etc.).

All of this genre subversiveness is never made awkwardly overt; rather, it exists just below the movie’s candy-colored surface, which is textured with outlandish couture, beautiful homes, chatty Valley speak, and something that is missing far too often in teen films: a sneaky love of life. Clueless never takes itself seriously, especially with its exaggerated tone and visuals, yet it has some real insight into both teen life and human nature in general. In other words, it’s everything you should expect a good teen comedy to be.

Copyright © 2020 James Kendrick

Thoughts? E-mail James Kendrick

All images copyright © Paramount Home Entertainment